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SML0777

Sigma-Aldrich

Oltipraz metabolite M2

≥98% (HPLC)

Synonym(s):

7-Methyl-6,8-bis(methylthio)-pyrrolo[1,2-a]pyrazine

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About This Item

Empirical Formula (Hill Notation):
C10H12N2S2
CAS Number:
84201-40-1
Molecular Weight:
224.35
UNSPSC Code:
12352200
NACRES:
NA.77
Pricing and availability is not currently available.

Quality Level

100

Assay

≥98% (HPLC)

form

powder

storage condition

protect from light

color

white to light brown

solubility

DMSO: 10 mg/mL, clear

storage temp.

2-8°C

SMILES string

S(C)c1[n]2c(c(c1C)SC)C=NC=C2

InChI

1S/C10H12N2S2/c1-7-9(13-2)8-6-11-4-5-12(8)10(7)14-3/h4-6H,1-3H3

InChI key

MYLBTCQBKAKUTJ-UHFFFAOYSA-N

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Show Differences

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This Item
O9389SML1200SML1816
Oltipraz metabolite M2 ≥98% (HPLC)

SML0777

Oltipraz metabolite M2

Oltipraz ≥98% (HPLC), powder

O9389

Oltipraz

RO8191 ≥98% (HPLC)

SML1200

RO8191

ABC44 ≥98% (HPLC)

SML1816

ABC44

form

powder

form

powder

form

powder

form

powder

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

solubility

DMSO: 10 mg/mL, clear

solubility

DMSO: >20 mg/mL

solubility

DMSO: 0.5 mg/mL, clear (warmed)

solubility

DMSO: 10 mg/mL, clear

storage condition

protect from light

storage condition

protect from light

storage condition

-

storage condition

-

Biochem/physiol Actions

M2 is a metabolite of the chemopreventive agent oltipraz. Oltipraz metabolite M2 has been shown to inhibit liver steatosis by inhibiting lipogenesis and enhancing mitochondrial function, including fuel oxidation. Oltipraz metabolite M2 acts as a potent inhibitor of LXRa transcriptional activity, and also AMPK activator inducing the phosphorylation of AMPK.
M2 is a metabolite of the chemopreventive agent oltipraz; LXRa inhibitor; AMPK activator.

Features and Benefits

This compound is featured on the AMPKs page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Other Notes

Light sensitive and air sensitive.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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    Lot/Batch Number
    083M4606V

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    H J Prochaska et al.
    Molecular pharmacology, 48(1), 15-20 (1995-07-01)
    Oltipraz, an inhibitor of human immunodeficiency virus type 1 replication in vitro (ED50 approximately 10 microM), undergoes extensive metabolism in vivo. Most of the orally administered drug undergoes opening of the dithiolethione ring, reduction, recyclization, and methylation to form 7-methyl-6,8-bis(methylthio)pyrrolo[1,2-a]pyrazine
    S G Kim et al.
    Clinical pharmacology and therapeutics, 88(3), 360-368 (2010-07-29)
    Oltipraz is a potential candidate drug for the treatment of liver fibrosis (LF) and liver cirrhosis (LC). The pharmacokinetics of oltipraz and its major rearranged metabolite (7-methyl-6,8-bis(methylthio)H-pyrrolo[1,2-a]pyrazine (RM)) were evaluated after single-dose (30-90 mg) and multiple-dose (60 mg b.i.d. or

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    AMPKs

    The AMP-activated protein kinase (AMPK) acts as a sensor of cellular energy status. AMPK exists as heterotrimeric complexes comprising a catalytic α subunit and regulatory β and γ subunits.

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